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Method for producing thioester group-containing organosilicon compound, thioester group-containing organosilicon compound, compounding agent for rubber, rubber composition, and tire

a technology of organosilicon and thioester group, which is applied in the direction of organic chemistry, transportation and packaging, and rolling resistance optimization, can solve the problems of low workability, high cost, and inability to achieve the desired low fuel consumption of the rubber composition of the tire, so as to achieve the desired low fuel consumption, reduce scorching, and improve the effect of reactivity and dispersibility

Active Publication Date: 2014-06-17
SHIN ETSU CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides an improved method for producing a thioester group-containing organosilicon compound which generates reduced byproducts and has higher production efficiency compared to prior art methods. This organosilicon compound has improved reactivity and dispersibility near silica, simultaneously with reduced scorching during rubber vulcanization and reduced environmental load due to reduced VOC generation. Additionally, the rubber composition containing this organosilicon compound as its compounding agent for rubber exhibits reduced hysteresis loss.

Problems solved by technology

However, silica-reinforced rubber compositions suffered from high viscosity before the vulcanization, and this resulted in the need of multiple-step kneading and low workability despite the decrease of the rolling resistance and the increase of the wet grip of the tire.
Accordingly, a rubber composition prepared by simply blending an inorganic filler such as silica suffered from the problems of insufficient filler dispersion which resulted in the drastic loss of strength at breakage and abrasion resistance.
However, a rubber composition for tire which has realized the desired low fuel consumption has not yet been realized by the use of such sulfur-containing organosilicon compounds.
Examples of the remaining problems include higher cost compared to the sulfide-type compound and insufficient productivity due to the complicated production method.

Method used

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  • Method for producing thioester group-containing organosilicon compound, thioester group-containing organosilicon compound, compounding agent for rubber, rubber composition, and tire
  • Method for producing thioester group-containing organosilicon compound, thioester group-containing organosilicon compound, compounding agent for rubber, rubber composition, and tire
  • Method for producing thioester group-containing organosilicon compound, thioester group-containing organosilicon compound, compounding agent for rubber, rubber composition, and tire

Examples

Experimental program
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Effect test

example 1

[0090]A 1 L separable flask equipped with an agitator, a reflux condenser, a dropping funnel, and a thermometer was charged with 102.1 g (1.0 mol) of acetic anhydride, 1.0 g (0.01 mol) of N,N-dimethylaminopyridine, and 300 g of toluene, and the mixture was heated to 70° C. in an oil bath. To this mixture, 243.2 g (1.0 mol) of γ-mercaptopropyltriethoxysilane (KBE-803 manufactured by Shin-Etsu Chemical Co., Ltd.) was added dropwise, and then, the mixture was stirred for 2 hours by heating to 70° C. Reaction was completed after confirming the complete disappearance of the peak from the mercaptosilane of the starting material and appearance of the peak from the thioesterified moiety by GC. The reaction solution was distilled at reduced pressure to remove toluene and obtain a colorless transparent liquid (yield, 310.7 g). The thus obtained reaction product had a viscosity of 2.7 mm2 / s, a specific weight of 1.026, and a refractive index of 1.477. 1H NMR spectrum revealed that the reaction...

example 2

[0092]A 1 L separable flask equipped with an agitator, a reflux condenser, a dropping funnel, and a thermometer was charged with 270.4 g (1.0 mol) of octanoic anhydride, 1.0 g (0.01 mol) of N,N-dimethylaminopyridine, and 300 g of toluene, and the mixture was heated to 70° C. in an oil bath. To this mixture, 243.2 g (1.0 mol) of γ-mercaptopropyltriethoxysilane (KBE-803 manufactured by Shin-Etsu Chemical Co., Ltd.) was added dropwise, and then, the mixture was stirred for 2 hours by heating to 70° C. Reaction was completed after confirming the complete disappearance of the peak from the mercaptosilane of the starting material and appearance of the peak from the thioesterified moiety by GC. The reaction solution was distilled at reduced pressure to remove toluene and obtain a yellow transparent liquid (yield, 416.1 g). The thus obtained reaction product had a viscosity of 250.7 mm2 / s, a specific weight of 1.031, and a refractive index of 1.484. 1H NMR spectrum revealed that the reactio...

example 3

[0094]A 1 L separable flask equipped with an agitator, a reflux condenser, a dropping funnel, and a thermometer was charged with 100.1 g (1.0 mol) of succinic anhydride, 1.0 g (0.01 mol) of N,N-dimethylaminopyridine, and 300 g of toluene, and the mixture was heated to 70° C. in an oil bath. To this mixture, 243.2 g (1.0 mol) of γ-mercaptopropyltriethoxysilane (KBE-803 manufactured by Shin-Etsu Chemical Co., Ltd.) was added dropwise, and then, the mixture was stirred for 2 hours by heating to 70° C. Reaction was completed after confirming the complete disappearance of the peak from the mercaptosilane of the starting material by GC. The reaction solution was distilled at reduced pressure to remove toluene and obtain a colorless transparent liquid (yield, 326.2 g). The thus obtained reaction product had a viscosity of 232 mm2 / s, a specific weight of 1.029, and a refractive index of 1.483. 1H NMR spectrum revealed that the reaction product was a mixture of the compounds represented by t...

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Abstract

A new method for producing a thioester group-containing organosilicon compound by a convenient reaction with dramatically improved workability generating reduced byproduct is provided. The method comprises reacting an organosilicon compound having a hydrolyzable silyl group and mercapto group with a carboxylic anhydride. Also provided are an organosilicon compound having a hydrolyzable silyl group, a thioester group, and carboxyl group in the same molecule capable of remarkably reducing hysteresis loss of the cured rubber composition; a compounding agent for rubber containing such organosilicon compound; a rubber composition prepared by blending such compounding agent for rubber; and a tire produced by using the cured rubber composition are also provided.

Description

CROSS-REFERENCE TO RELATED APPLICATION[0001]This non-provisional application claims priority under 35 U.S.C. §119(a) on Patent Application No. 2011-109413 filed in Japan on May 16, 2011, the entire contents of which are hereby incorporated by reference.TECHNICAL FIELD[0002]This invention relates to a novel method for producing an organosilicon compound having a hydrolyzable silyl group and a thioester group in its molecule with a reduced byproduct generation. This invention also relates to an organosilicon compound containing a hydrolyzable silyl group, a thioester group, and carboxyl group in the same molecule, a compounding agent for rubber containing such organosilicon compound, a rubber composition prepared by blending such compounding agent for rubber, and a tire prepared by using such rubber composition.BACKGROUND ART[0003]Sulfur-containing organosilicon compounds are useful as a component for blending in silica-reinforced rubber composition used for the production of a tire. ...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C08K5/548C08L7/00C07F7/18
CPCC08K3/36C08K5/548C08G77/045C08G77/28Y02T10/862C08L21/00
Inventor TSUCHIDA, KAZUHIROHIROKAMI, MUNENAO
Owner SHIN ETSU CHEM IND CO LTD
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